Indole-4-boronic acid pinacol ester Chemical Properties

Melting point:

120-125 °C(lit.)

Boiling point:

396.0±15.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

16.83±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-6-5-7-12-10(11)8-9-16-12/h5-9,16H,1-4H3

InChIKey

QDCIXBBEUHMLDN-UHFFFAOYSA-N

SMILES

N1C2=C(C(B3OC(C)(C)C(C)(C)O3)=CC=C2)C=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933299090

Indole-4-boronic acid pinacol ester Usage And Synthesis

Chemical Properties

White powder

Uses

Indole-4-boronic acid, pinacol ester

Synthesis

The general procedure for the synthesis of 4-indoleboronic acid pinacol ester from 4-bromoindole and biboronic acid pinacol ester is as follows: (a) Preparation of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole. 4-Bromoindole (1.00 g, 5.10 mmol), bis(pinacolato)diboron (1.68 g, 6.63 mmol), potassium acetate (1.44 g, 15.3 mmol), and dichlorodi(diphenylphosphine)palladium(II) dichloride dichloromethane complex (206 mg, 0.26 mmol) were added to a 50 mL round-bottomed flask under argon gas protection. Anhydrous dimethyl sulfoxide (16 mL) was then added and the reaction mixture was heated at 90 °C with stirring for 4 hours. After completion of the reaction, it was cooled to room temperature, filtered through a short column of silica gel and the filter cake was washed with tert-butyl methyl ether (2 x 50 mL). The filtrates were combined, washed with saturated saline (3 x 50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by fast column chromatography (ethyl acetate/heptane, 1:4) to afford 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole as a white solid (1.24 g, quantitative yield).

References

[1] Patent: US2008/280891, 2008, A1. Location in patent: Page/Page column 30
[2] Patent: WO2008/8059, 2008, A1. Location in patent: Page/Page column 81-82
[3] Organic Letters, 2012, vol. 14, # 2, p. 600 - 603
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2496 - 2500
[5] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276

Indole-4-boronic acid pinacol ester(388116-27-6)Related Product Information

• Tris(trimethylsilyl)phosphate
• Indole-3-butyric acid
• Pinacol
• Indometacin
• Indole
• Indole-3-acetic acid
• Bis(pinacolato)diboron
• Indole-7-boronic acid pinacol ester
• 6-HYDROXYMETHYLINDOLE
• Methyl indole-6-carboxylate
• INDOLE-5-METHANOL
• INDOLE-7-METHANOL
• Indole-5-carboxaldehyde
• Indole-4-carboxaldehyde
• Indoline-2-carboxylic acid
• TRYPTANTHRIN
• INDOLE-2-ACETIC ACID
• Indole-7-carboxylic acid ethyl ester